CH629482A5 - Process for the preparation of 1-(4-isopropylmercaptophenyl)-2-N-octylamino-propanol - Google Patents
Process for the preparation of 1-(4-isopropylmercaptophenyl)-2-N-octylamino-propanol Download PDFInfo
- Publication number
- CH629482A5 CH629482A5 CH678578A CH678578A CH629482A5 CH 629482 A5 CH629482 A5 CH 629482A5 CH 678578 A CH678578 A CH 678578A CH 678578 A CH678578 A CH 678578A CH 629482 A5 CH629482 A5 CH 629482A5
- Authority
- CH
- Switzerland
- Prior art keywords
- octylamino
- preparation
- propanol
- phenyl
- isopropylmercapto
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000005903 acid hydrolysis reaction Methods 0.000 claims abstract description 3
- -1 4-isopropylmercapto-phenyl residue Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- ZJNGCHWVIQXKRC-UHFFFAOYSA-N 1-(octylamino)propan-1-ol Chemical compound CCCCCCCCNC(O)CC ZJNGCHWVIQXKRC-UHFFFAOYSA-N 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract description 2
- 239000012279 sodium borohydride Substances 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- BFCDFTHTSVTWOG-YLJYHZDGSA-N (1S,2R)-2-(octylamino)-1-[4-(propan-2-ylthio)phenyl]-1-propanol Chemical compound CCCCCCCCN[C@H](C)[C@@H](O)C1=CC=C(SC(C)C)C=C1 BFCDFTHTSVTWOG-YLJYHZDGSA-N 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
- 241000023586 Chetone Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000013566 allergen Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229960003967 suloctidil Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25580/77A IT1082122B (it) | 1977-07-11 | 1977-07-11 | Processo per la preparazione dell'1-(4-isopropilmercapto-fenil)-2-n.ottilammino-propanolo |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH629482A5 true CH629482A5 (en) | 1982-04-30 |
Family
ID=11217152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH678578A CH629482A5 (en) | 1977-07-11 | 1978-06-22 | Process for the preparation of 1-(4-isopropylmercaptophenyl)-2-N-octylamino-propanol |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5419927A (de) |
| AT (1) | AT356080B (de) |
| CA (1) | CA1106410A (de) |
| CH (1) | CH629482A5 (de) |
| IT (1) | IT1082122B (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU83039A1 (fr) * | 1980-12-24 | 1982-07-07 | Continental Pharma | Procedes de synthese du 1-(4 isopropylthiophenyl)-2-n octylaminopropanol |
| AT380874B (de) * | 1980-12-24 | 1986-07-25 | Continental Pharma | Verfahren zur herstellung von 1-(4-isopropylthiophenyl)-2-n.octyl-amino-propanol, dessen saeureadditionssalzen und estern |
| AT380873B (de) * | 1980-12-24 | 1986-07-25 | Continental Pharma | Verfahren zur herstellung von 1-(4-isopropylthiophenyl)-2-n.octyl-amino -propanol, dessen saeureadditionssalzen und estern |
-
1977
- 1977-07-11 IT IT25580/77A patent/IT1082122B/it active
-
1978
- 1978-06-22 CH CH678578A patent/CH629482A5/it not_active IP Right Cessation
- 1978-06-29 CA CA306,545A patent/CA1106410A/en not_active Expired
- 1978-07-04 JP JP8185878A patent/JPS5419927A/ja active Granted
- 1978-07-05 AT AT486078A patent/AT356080B/de active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5419927A (en) | 1979-02-15 |
| ATA486078A (de) | 1979-09-15 |
| IT1082122B (it) | 1985-05-21 |
| CA1106410A (en) | 1981-08-04 |
| AT356080B (de) | 1980-04-10 |
| JPS5725545B2 (de) | 1982-05-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |